1,2-Dichloroethane → {4-[3-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyrimidin-2-yl}-diethyl-amine

HRID 2069426Notes

Reaction equation

HRID 2069426 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[C:4]1[N:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[C:6]([CH3:13])[N:5]=1)[CH3:2].[CH2:16]([O:23][C:24]1[C:33]([CH3:34])=[CH:32][C:27]([C:28]([NH:30]O)=[NH:29])=[CH:26][C:25]=1[CH2:35][CH3:36])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CCOC(C)=O.O1CCOCC1>[CH2:16]([O:23][C:24]1[C:33]([CH3:34])=[CH:32][C:27]([C:28]2[N:30]=[C:10]([C:8]3[CH:7]=[C:6]([CH3:13])[N:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH2:14][CH3:15])[N:9]=3)[O:12][N:29]=2)=[CH:26][C:25]=1[CH2:35][CH3:36])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 242773182-(Diethylamino)-6-methylpyrimidine-4-carboxylic acidHCID 178436627HCID 178436627, compound

Product 1

HCID 68510556{4-[3-(4-Benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyrimidin-2-yl}-diethyl-amineYield 35%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 2-diethylamino-6-methyl-pyrimidine-4-carboxylic acid (5.56 g, 27.0 mmol mmol) and 4-benzyloxy-3-ethyl-N-hydroxy-5-methyl-benzamidine (7.69 g, 27 mmol) in DMF (80 mL), EDC (6.74 g, 35.2 mmol) and HOBt (4.75 g, 35.2 mmol) are added at 0° C. Stirring is continued at rt for 2 h and the reaction mixture is then diluted with EtOAc and washed with sat. aq. NaHCO3. The aq. phase is extracted with EtOAc and the combined org. extracts are dried over MgSO4, filtered and evaporated to give a brown oil. The oil is dissolved in dioxane (30 mL) and the solution is heated to 85° C. for 18 h. The reaction mixture is evaporated and purified by CC (eluting with Heptane/EA 9:1) to afford {4-[3-(4-benzyloxy-3-ethyl-5-methyl-phenyl)-[1,2,4]oxadiazol-5-yl]-6-methyl-pyrimidin-2-yl}-diethyl-amine as a yellow oil (4.3 g, 35%); LC-MS: tR=1.35; [M+H]+=458.48.

Workup

  1. washwashed with sat. aq. NaHCO3
  2. extractionThe aq. phase is extracted with EtOAc
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown oil
  7. customThe reaction mixture is evaporated
  8. custompurified by CC (eluting with Heptane/EA 9:1)

Sources & evidence

ORD record
ord-77b47cd067c9455292c122cdad4f4504
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

Loading…